Originally aired as episode 200 on April 5, 2022.

With a remarkable 14 nominations and six wins across the Emmys, Grammys, Olivier, and Tony Awards, Patti LuPone is a force in the entertainment industry. Her illustrious career includes 27 Broadway credits, most notably her Tony Award-winning roles as Eva Perón in Evita and Rose in the 2008 revival of Gypsy. Other significant Broadway appearances include Anything Goes, Sweeney Todd, Noises Off, Women on the Verge of a Nervous Breakdown, War Paint, Working, Oliver!, The Robber Bridegroom, and The Beggar's Opera.

LuPone has also made her mark on the London stage, originating roles in Les Misérables, The Cradle Will Rock, Sunset Boulevard, and starring in the West End revival of Company. Beyond the stage, her extensive career in television and film includes performances in Driving Miss Daisy, Frasier, Will & Grace, Ugly Betty, 30 Rock, Glee, American Horror Story, Girls, Penny Dreadful, and Life Goes On. A versatile performer, LuPone has also lent her talents to voiceover work, cabaret performances, and regular appearances with the New York Philharmonic, contributing to 22 albums. She is the first American to win an Olivier Award and has been inducted into the American Theater Hall of Fame. Currently, she stars in the Broadway revival of Company.

In this episode, LuPone reflects on her introduction to Gypsy, recalling her role as Louise in high school, and shares the story of how she was once banned from working on any of Arthur Laurents' projects before ultimately winning a Tony Award for her portrayal of Rose. She opens up about the challenges she faced during the COVID-19 shutdown, discussing how the lack of purpose impacted her deeply. She also highlights the strong sense of camaraderie and support among the cast and crew of Company, forged through their shared experiences during the pandemic. LuPone delves into her rehearsal process, explaining why she completes all her preparation in the rehearsal room so that she and the audience can enjoy the spontaneity and energy of live performance. Additionally, she reveals why she makes it a point to look at the audience every night.

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